Indole alkaloids: dihydroteleocidin B, teleocidin, and lyngbyatoxin A as members of a new class of tumor promoters.
Dihydroteleocidin B, which is a derivative of teleocidin from Streptomyces, showed potent tumor-promoting activity in vivo when painted on mouse skin. Although the chemical structure of dihydroteleocidin B is entirely different from those of phorbol esters, the tumor-promoting activity of dihydroteleocidin B was found to be comparable to that of 12-O-tetradecanoylphorbol 13-acetate (TPA) in vivo. Teleocidin from Streptomyces and lyngbyatoxin A and debromoaplysiatoxin from the marine blue-green alga Lyngbya majuscula induced ornithine decarboxylase activity when painted on mouse skin, their effects being similar to those of dihyroteleocidin B and TPA. 13-cis-Retinoic acid inhibited this ornithine decarboxylase induction when painted on the skin 1 hr before these natural products. These three compounds produced adhesion of human promyelocytic leukemia cells (HL-60) to the flasks and inhibited differentiation of Friend erythroleukemia cells induced by dimethyl sulfoxide. The in vitro biological potencies of teleocidin and lyngbyatoxin A were almost as great as those of dihydroteleocidin B and TPA, but that of debromoaplysiatoxin was much weaker.
D015127:9,10-Dimethyl-1,2-benzanthracene; D000470:Alkaloids; D000818:Animals; D002273:Carcinogens; D003043:Cocarcinogenesis; D003885:Dermotoxins; D004790:Enzyme Induction / Q000187:drug effects; D005260:Female; D007509:Irritants; D008235:Lyngbya Toxins; D008387:Marine Toxins; D051379:Mice; D009374:Neoplasms, Experimental / Q000139:chemically induced; D009955:Ornithine Decarboxylase / Q000096:biosynthesis; D012878:Skin Neoplasms / Q000139:chemically induced; D013329:Structure-Activity Relationship
D000470:Alkaloids; D002273:Carcinogens; D003885:Dermotoxins; D007509:Irritants; D008235:Lyngbya Toxins; D008387:Marine Toxins; C022176:teleocidins; D015127:9,10-Dimethyl-1,2-benzanthracene; C022229:dihydroteleocidin B; D009955:Ornithine Decarboxylase; C019457:lyngbyatoxin A